35607-20-6

Basic information

• Product Name: Avridine
• Synonyms: Avridine;2,2'-[[3-(Dioctadecylamino)propyl]imino]bisethanol;2,2'-[[3-(Dioctadecylamino)propyl]imino]diethanol;CP-20961;N,N-Dioctadecyl-N',N'-bis(2-hydroxyethyl)-1,3-diaminopropane;N,N-Dioctadecyl-N',N'-bis(2-hydroxyethyl)propanediaMine
• CAS NO: 35607-20-6
• Molecular Formula: C43H90N2O2
• Molecular Weight: 667.196
• Product Categories: Aliphatics;Amines;Intermediates & Fine Chemicals;Pfizer Compounds;Pharmaceuticals
• Mol File: 35607-20-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 717.6°Cat760mmHg
• Flash Point: 294.3°C
• Appearance: white to off-white/
• Density: 0.892g/cm³
• Vapor Pressure: 8.77E-24mmHg at 25°C
• Refractive Index: 1.478
• Storage Temp.: Store at RT
• Solubility: DMSO: ≥5mg/mL (with warming to 60 °C for 5 minutes)
• CAS DataBase Reference: Avridine(CAS DataBase Reference)
• NIST Chemistry Reference: Avridine(35607-20-6)
• EPA Substance Registry System: Avridine(35607-20-6)

Safety Data

• WGK Germany: 3
• RTECS: KK7243000
• Hazardous Substances Data: 35607-20-6(Hazardous Substances Data)

Usage

Description

Avridine is a potent synthetic non-immunogenic adjuvant that possesses immunomodulatory and interferon-inducing properties. It is known for its ability to induce arthritis in most rat strains, making it a significant compound in the field of immunology and drug development.

Uses

Used in Pharmaceutical Industry:
Avridine is used as an immunomodulator for its ability to modulate the immune system and enhance the body's response to various diseases and conditions.
Used in Research Applications:
Avridine is used as a research tool for studying the mechanisms of arthritis induction and immune system responses in rats, providing valuable insights into the development of new therapeutic strategies for autoimmune and inflammatory diseases.
Used in Drug Development:
Avridine is used as a potential candidate for the development of new drugs targeting autoimmune and inflammatory conditions, given its immunomodulatory and interferon-inducing properties. Its ability to induce arthritis in rats makes it a useful model for testing the efficacy of new treatments.

Originator

Avridine,Chemical

Manufacturing Process

N,N-Dioctadecyl-1,3-propanediamine: A). A two-gallon autoclave is charged with 3-(dioctadecylamino)propionitrile (100 g), ethanol (3750 ml) containing anhydrous ammonia (100 g) and Raney nickel (20 g dry basis) and purged with nitrogen, then with hydrogen. It is then sealed and the hydrogen pressure raised to 250 psi. The autoclave is agitated, the temperature raised to 70°C and the mixture held at this temperature for 1.5 hours at which time hydrogen absorption has ceased. The autoclave is cooled to 20°C, vented, and the contents removed. The catalyst is filtered off, washed with ethanol, and the combined washings and reaction mixture concentrated in vacuum to a viscous green-yellow oil (82 g) which solidified upon standing, MP: 39°-41°C. 3-(Dioctadecylamino)propionitrile is prepared by refluxing a mixture of dioctadecylamine (200 g) and acrylonitrile (1903.8 ml) for eighteen hours. The mixture is then concentrated to a waxy semi-solid which is slurried in acetone, filtered, and air dried overnight. B). The monoacyl derivatives of N,N-dioctadecyl-1,3-propanediamine are prepared as follows: To a solution of methylene chloride (500 ml per 0.1 mole of reactants) containing equimolar amounts of N,N-dioctadecyl-1,3-propanediamine and triethylamine and cooled in an ice-bath is added an equimolar amount of the appropriate acyl chloride in methylene chloride (25 ml per 0.1 mole of acyl chloride) over a period of 15 minutes. The mixture is stirred for ten minutes then brought to room temperature and stirred for one hour. The methylene chloride phase is separated and extracted with water (3x25 ml). The water is in turn extracted with methylene chloride (2x25 ml) and the combined methylene chloride phases dried (Na2SO4) then evaporated under reduced pressure. The residue is taken up in benzene and the solution passed through a silica gel column. The column is eluted with benzene, then with benzene containing increasing amounts of ethyl acetate, e.g., 5, 10, 25, and 50 %. The eluate is subjected to thin layer chromatography (ethyl acetate) and those fractions, which show only one spot, combined and evaporated to give N,N-dioctadecyl-N',N'-bis(2-hydroxyethyl)propanediamine M.P. 48.5°-49°C.

Therapeutic Function

Antiviral

Biological Activity

Non-immunogenic adjuvant; used to induce arthritis in Lewis (LEW) and DA rats.

InChI:InChI=1/C43H90N2O2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-36-44(38-35-39-45(40-42-46)41-43-47)37-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h46-47H,3-43H2,1-2H3

Upstream product

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Relevant articles and documents

Synthetic immunogen

The present invention concerns novel immunogens. These immunogens comprise novel compounds which consist of an antigen or antigenic determinant couple dot an amphiphilic adjuvant molecule and optionally also free amphiphilic adjuvant molecules. An advantageous features of these novel immunogens is the presence of both an excellent immunogen activity as well as a pronounced adjuvant activity in a single complex.

Xylene-diamines as antiviral agents

Compounds of the formula STR1 or a non-toxic acid addition salt thereof wherein R1 is alkyl of from 1 to 20 carbon atoms; R2 is alkyl of from 12 to 20 carbon atoms; R3 is selected from the group consisting of hydrogen and hydroxyalkyl of from 2 to 8 carbon atoms; and R4 is selected from the group consisting of hydrogen, alkyl of from 1 to 8 carbon atoms and hydroxyalkyl of from 2 to 8 carbon atoms, said compounds are useful for combating viral infections in vertebrate animals.